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| 4-tert-Butylcyclohexanone Basic information |
| 4-tert-Butylcyclohexanone Chemical Properties |
| Melting point | 47-50 °C (lit.) | | Boiling point | 113-116 °C/20 mmHg (lit.) | | density | 0.893 | | vapor pressure | 7.91-14.2Pa at 20-25℃ | | refractive index | 1.4570 (estimate) | | Fp | 205 °F | | storage temp. | Sealed in dry,Room Temperature | | solubility | Chloroform (Slightly), Methanol (Slightly) | | form | Crystalline Powder | | color | White to almost white | | Water Solubility | Soluble in alcohol, ethanol (0.5g/10 mL). Insoluble in water. | | BRN | 507309 | | InChIKey | YKFKEYKJGVSEIX-UHFFFAOYSA-N | | LogP | 2.91 | | CAS DataBase Reference | 98-53-3(CAS DataBase Reference) | | NIST Chemistry Reference | Cyclohexanone, 4-(1,1-dimethylethyl)-(98-53-3) | | EPA Substance Registry System | Cyclohexanone, 4-(1,1-dimethylethyl)- (98-53-3) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 2 | | RTECS | GW1140000 | | TSCA | Yes | | HS Code | 29142990 | | toxicity | Both the acute oral LD50 value in rats and the acute dermal LD50 value in rabbits were reported to be 5 g/kg |
| 4-tert-Butylcyclohexanone Usage And Synthesis |
| Chemical Properties | WHITE TO ALMOST WHITE CRYSTALLINE POWDER | | Occurrence | Has apparently not been reported to occur in nature. | | Uses | 4-tert-Butylcyclohexanone is used as a perfuming agents and in cosmetic. | | Preparation | By hydrogenation of p-ferr-butylphenol. Care must be taken that no free p-tert-butylphenol remains, because it is a sensitizer and depigmenting agent(Opdyke, 1974). | | Preparation | N-Chlorosuccinimide (NCS) (8.0 g, 0.060 mol) and toluene (200 mL) were cooled to 0 C° in a 1-L, threenecked, round-bottomed flask equipped with a mechanical stirrer, a thermometer, a dropping funnel, and an argon inlet tube. Dimethyl sulfoxide (6.0 mL, 0.10 mol) was added and the mixture was cooled to -25 C° using a tetrachloromethane/dryice bath. A solution of 4-tert-butylcyclohexanol (6.24 g, 0.04 mol; mixture of E and Z isomers) in toluene (40 mL) was added dropwise over 5 min, stirring was continued for 2 h at -25 C°, and then a solution of triethylamine (6.0 g, 0.06 mol) in toluene (10 mL) was added dropwise over 3 min. The cooling bath was removed, and, after 5 min, diethyl ether (400 mL) was added. The organic phase was washed with 1% aq. hydrochloric acid (100 mL) and then with water (2 × 100 mL), and dried over anhydrous magnesium sulfate. The solvents were evaporated under reduced pressure, and the residue was transferred to a 50-mL, round-bottomed flask and bulb-to-bulb distilled at 120 C° (25 mmHg) to yield 5.72 g (93%) of 4-tertbutylcyclohexanone 1794; mp 41–45 C°. Recrystallization from petroleum ether at -20 C° gave an 88% recovery of 1794 with mp 45–46 C°. | | Synthesis Reference(s) | Chemistry Letters, 24, p. 507, 1995Journal of the American Chemical Society, 94, p. 7586, 1972 DOI: 10.1021/ja00776a056Tetrahedron Letters, 16, p. 3775, 1975 | | Purification Methods | Purify it via the semicarbazone (crystallised from EtOH with m 203-205o), hydrolyse this with dilute HCl and steam distil it. The distillate is extracted into Et2O, dried, evaporated and the residue is recrystallised from pentane, aqueous EtOH or EtOH [Houlihan J Org Chem 27 3860 1962]. The oxime recrystallises from 1,2-dichloropropane and has m 137.5-138.5o. [Harvill et al. J Org Chem 15 58 1950, Beilstein 7 IV 82.] |
| 4-tert-Butylcyclohexanone Preparation Products And Raw materials |
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